I cannot answer some of your questions but generally the consensus is that it is far easier to buy and register a bike in Chile and then legally leave Chile to other countries. There are some very extensive threads on the HUBB explaining in detail how to do this.
Registering in Argentina as you appear to be aware of is rather restrictive and its not a popular place for foreigners to buy a bike legally.
The illegal option you mentioned is popular and again lots of threads on it. I believe the popular option is to take the bike on the ferry to Uruguay and change title in no mans land.
I'm sure others will chip in on the computer issue when entering back into Chile or Argentina but I believe from reading lots of posts is that the most important thing is that the paperwork is done correctly. Photoshop is the word that gets thrown around a lot. If you are open to doing it on a small Honda or suzuki that will cruise at between 90-100 km hour depending on your weight and luggage you can pick up a new, legally registered bike in Chile, new for well under $2,000 US
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